of 39
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
1
Supporting Information:
X
-
Ray Crystallography Data
Enantioselective Nickel
-
Catalyzed
a
-
Spirocyclization of Lactones
Allison M. Stanko, Melissa Ramirez, Adrian J. de Almenara, Scott C. Virgil, Brian M. Stoltz*
Warren and Katharine Schlinger
Laboratory of Chemistry and Chemical Engineering, Division of
Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California
91125, United States.
*stoltz@caltech.edu
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
2
X
-
Ray Structure Determination
: Compound S26
Figure S1.
X
-
ray coordinate of c
ompound
S26
.
Ellipsoid contour % probability level: 50
.
Low
-
temperature diffraction data (
f
-
and
w
-
scans) were collected on a Bruker AXS D8
VENTURE KAPPA diffractometer coupled to a PHOTON
II CPAD
detector with Cu
K
a
radiation
(
l
= 1.54178 Å) from an I
μ
S micro
-
source for the structure of compound
V23214
. The structure
was solved by direct methods using SHELXS
i
and refined against
F
2
on all data by full
-
matrix
least squares with SHELXL
-
201
9
ii
using established refinement techniques.
iii
All non
-
hydrogen
atoms were refined anisotropically. All hydrogen atoms were included into the model at
geometrically ca
lculated positions and refined using a riding model. The isotropic displacement
parameters of all hydrogen atoms were fixed to 1.2 times the
U
value of the atoms they are linked
to (1.5 times for methyl groups).
Compound
V23214
crystallizes in the
orthorhombic
space group
P
2
1
2
1
2
1
with one
molecule in the asymmetric unit.
Table S1.
Crystal data and structure refinement for
S26
Empirical formula
C
18
H
15
NO
2
Formula weight
277.31
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
3
Temperature
100(2) K
Wavelength
1.54178 Å
Crystal system
Orthorhombic
Space group
P2
1
2
1
2
1
Unit cell dimensions
a = 8.4202(10) Å
a
= 90°.
b = 9.7385(14) Å
b
= 90°.
c = 17.3452(16) Å
g
= 90°.
Volume
1422.3(3) Å
3
Z
4
Density (calculated)
1.295 Mg/m
3
Absorption coefficient
0.677 mm
-
1
F(000)
584
Crystal size
0.200 x 0.150 x 0.100 mm
3
Theta range for data collection
5.100 to 74.489°.
Index ranges
-
10<=h<=10,
-
12<=k<=12,
-
21<=l<=21
Reflections collected
19589
Independent reflections
2899 [R(int) = 0.0515]
Completeness to theta = 67.679°
100.0 %
Absorption
correction
Semi
-
empirical from equivalents
Max. and min. transmission
0.7538 and 0.6485
Refinement method
Full
-
matrix least
-
squares on F
2
Data / restraints / parameters
2899 / 0 / 190
Goodness
-
of
-
fit on F
2
1.057
Final R indices [I>2sigma(I)]
R1 = 0.0288, wR2 = 0.0665
R indices (all data)
R1 = 0.0317, wR2 = 0.0683
Absolute structure parameter
-
0.04(11)
Extinction coefficient
n/a
Largest diff. peak and hole
0.168 and
-
0.138 e.Å
-
3
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
4
Table S2.
Atomic coordinates ( x 104) and equivalent isotropic displacement parameters (Å
2
x
10
3
)
for
S26
. U(eq) is defined as one third of the trace of the orthogonalized U
ij
tensor.
________________________________________________________________________________
x
y
z
U(eq)
________________________________________________________________________________
O(1)
315(2)
897(1)
2882(1)
25(1)
C(1)
1464(2)
1725(2)
2612(1)
21(1)
O(2)
1281(2)
2429(1)
2053(1)
27(1)
C(2)
827(2)
217(2)
3587(1)
29(1)
C(3)
2629(2)
319(2)
3588(1)
24(1)
C(4)
2946(2)
1624(2)
3116(1)
19(1)
C(5)
3011(2)
2888(2)
3644(1)
18(1)
N(1)
1747(2)
3294(2)
3973(1)
21(1)
C(13)
1732(2)
4426(2)
4487(1)
19(1)
C(14)
2020(2)
4222(2)
5269(1)
22(1)
C(15)
1932(2)
5318(2)
5778(1)
24(1)
C(16)
1524(3)
6608(2)
5516(1)
32(1)
C(17)
1182(3)
6795(2)
4741(1)
39(1)
C(18)
1294(3)
5717(2)
4224(1)
29(1)
C(6)
4674(2)
3378(2)
3651(1)
19(1)
C(7)
5420(2)
4372(2)
4107(1)
21(1)
C(8)
7036(2)
4596(2)
4005(1)
24(1)
C(9)
7895(2)
3856(2)
3458(1)
25(1)
C(10)
7150(2)
2883(2)
2997(1)
23(1)
C(11)
5540(2)
2648(2)
3098(1)
21(1)
C(12)
4511(2)
1651(2)
2661(1)
24(1)
Table S3.
Bond lengths [Å] and angles [°] for
S26
.
O(1)
-
C(1)
1.343(2)
O(1)
-
C(2)
1.457(2)
C(1)
-
O(2)
1.197(2)
C(1)
-
C(4)
1.527(2)
C(2)
-
C(3)
1.520(3)
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
5
C(2)
-
H(2A)
0.9900
C(2)
-
H(2B)
0.9900
C(3)
-
C(4)
1.536(2)
C(3)
-
H(3A)
0.9900
C(3)
-
H(3B)
0.9900
C(4)
-
C(5)
1.535(2)
C(4)
-
C(12)
1.537(2)
C(5)
-
N(1)
1.271(2)
C(5)
-
C(6)
1.480(2)
N(1)
-
C(13)
1.417(2)
C(13)
-
C(18)
1.388(3)
C(13)
-
C(14)
1.392(2)
C(14)
-
C(15)
1.387(3)
C(14)
-
H(14)
0.9500
C(15)
-
C(16)
1.380(3)
C(15)
-
H(15)
0.9500
C(16)
-
C(17)
1.388(3)
C(16)
-
H(16)
0.9500
C(17)
-
C(18)
1.383(3)
C(17)
-
H(17)
0.9500
C(18)
-
H(18)
0.9500
C(6)
-
C(7)
1.399(2)
C(6)
-
C(11)
1.399(3)
C(7)
-
C(8)
1.390(3)
C(7)
-
H(7)
0.9500
C(8)
-
C(9)
1.394(3)
C(8)
-
H(8)
0.9500
C(9)
-
C(10)
1.389(3)
C(9)
-
H(9)
0.9500
C(10)
-
C(11)
1.386(2)
C(10)
-
H(10)
0.9500
C(11)
-
C(12)
1.506(3)
C(12)
-
H(12A)
0.9900
C(12)
-
H(12B)
0.9900
C(1)
-
O(1)
-
C(2)
110.63(14)
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
6
O(2)
-
C(1)
-
O(1)
122.20(16)
O(2)
-
C(1)
-
C(4)
127.31(17)
O(1)
-
C(1)
-
C(4)
110.49(15)
O(1)
-
C(2)
-
C(3)
105.51(15)
O(1)
-
C(2)
-
H(2A)
110.6
C(3)
-
C(2)
-
H(2A)
110.6
O(1)
-
C(2)
-
H(2B)
110.6
C(3)
-
C(2)
-
H(2B)
110.6
H(2A)
-
C(2)
-
H(2B)
108.8
C(2)
-
C(3)
-
C(4)
103.09(15)
C(2)
-
C(3)
-
H(3A)
111.1
C(4)
-
C(3)
-
H(3A)
111.1
C(2)
-
C(3)
-
H(3B)
111.1
C(4)
-
C(3)
-
H(3B)
111.1
H(3A)
-
C(3)
-
H(3B)
109.1
C(1)
-
C(4)
-
C(5)
108.62(14)
C(1)
-
C(4)
-
C(3)
102.54(14)
C(5)
-
C(4)
-
C(3)
110.59(14)
C(1)
-
C(4)
-
C(12)
113.90(14)
C(5)
-
C(4)
-
C(12)
105.19(14)
C(3)
-
C(4)
-
C(12)
115.95(16)
N(1)
-
C(5)
-
C(6)
133.50(16)
N(1)
-
C(5)
-
C(4)
119.19(16)
C(6)
-
C(5)
-
C(4)
107.31(15)
C(5)
-
N(1)
-
C(13)
122.15(15)
C(18)
-
C(13)
-
C(14)
119.73(16)
C(18)
-
C(13)
-
N(1)
120.04(16)
C(14)
-
C(13)
-
N(1)
119.99(16)
C(15)
-
C(14)
-
C(13)
120.06(17)
C(15)
-
C(14)
-
H(14)
120.0
C(13)
-
C(14)
-
H(14)
120.0
C(16)
-
C(15)
-
C(14)
120.36(17)
C(16)
-
C(15)
-
H(15)
119.8
C(14)
-
C(15)
-
H(15)
119.8
C(15)
-
C(16)
-
C(17)
119.29(18)
C(15)
-
C(16)
-
H(16)
120.4
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
7
C(17)
-
C(16)
-
H(16)
120.4
C(18)
-
C(17)
-
C(16)
120.96(19)
C(18)
-
C(17)
-
H(17)
119.5
C(16)
-
C(17)
-
H(17)
119.5
C(17)
-
C(18)
-
C(13)
119.53(17)
C(17)
-
C(18)
-
H(18)
120.2
C(13)
-
C(18)
-
H(18)
120.2
C(7)
-
C(6)
-
C(11)
120.31(16)
C(7)
-
C(6)
-
C(5)
130.78(16)
C(11)
-
C(6)
-
C(5)
108.90(15)
C(8)
-
C(7)
-
C(6)
118.50(18)
C(8)
-
C(7)
-
H(7)
120.7
C(6)
-
C(7)
-
H(7)
120.7
C(7)
-
C(8)
-
C(9)
120.87(18)
C(7)
-
C(8)
-
H(8)
119.6
C(9)
-
C(8)
-
H(8)
119.6
C(10)
-
C(9)
-
C(8)
120.66(17)
C(10)
-
C(9)
-
H(9)
119.7
C(8)
-
C(9)
-
H(9)
119.7
C(11)
-
C(10)
-
C(9)
118.81(17)
C(11)
-
C(10)
-
H(10)
120.6
C(9)
-
C(10)
-
H(10)
120.6
C(10)
-
C(11)
-
C(6)
120.84(17)
C(10)
-
C(11)
-
C(12)
127.28(17)
C(6)
-
C(11)
-
C(12)
111.88(15)
C(11)
-
C(12)
-
C(4)
104.23(14)
C(11)
-
C(12)
-
H(12A)
110.9
C(4)
-
C(12)
-
H(12A)
110.9
C(11)
-
C(12)
-
H(12B)
110.9
C(4)
-
C(12)
-
H(12B)
110.9
H(12A)
-
C(12)
-
H(12B)
108.9
_____________________________________________________________
Symmetry transformations used to generate equivalent atoms:
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
8
Table S4
. Anisotropic displacement parameters (Å
2
x 10
3
) for
S26
. The anisotropic
displacement factor exponent takes the form:
-
2
p
2
[
h
2
a*
2
U
11
+ ... + 2 h k a* b* U
12
]
______________________________________________________________________________
U
11
U
22
U
33
U
23
U
13
U
12
______________________________________________________________________________
O(1)
22(1)
27(1)
27(1)
-
2(1)
-
3(1)
-
2(1)
C(1)
22(1)
20(1)
20(1)
-
6(1)
-
1(1)
1(1)
O(2)
34(1)
27(1)
21(1)
0(1)
-
6(1)
4(1)
C(2)
32(1)
27(1)
27(1)
3(1)
0(1)
-
7(1)
C(3)
30(1)
21(1)
20(1)
0(1)
-
3(1)
1(1)
C(4)
19(1)
21(1)
18(1)
-
2(1)
-
1(1)
1(1)
C(5)
20(1)
20(1)
14(1)
2(1)
-
2(1)
-
1(1)
N(1)
18(1)
24(1)
21(1)
-
2(1)
-
1(1)
0(1)
C(13)
15(1)
22(1)
20(1)
-
2(1)
1(1)
-
2(1)
C(14)
23(1)
22(1)
22(1)
1(1)
0(1)
1(1)
C(15)
29(1)
27(1)
17(1)
-
2(1)
2(1)
-
3(1)
C(16)
46(1)
23(1)
27(1)
-
8(1)
1(1)
-
1(1)
C(17)
62(2)
19(1)
35(1)
2(1)
-
7(1)
4(1)
C(18)
40(1)
25(1)
21(1)
3(1)
-
6(1)
-
2(1)
C(6)
19(1)
20(1)
17(1)
4(1)
0(1)
0(1)
C(7)
22(1)
21(1)
20(1)
3(1)
-
2(1)
0(1)
C(8)
23(1)
22(1)
27(1)
5(1)
-
5(1)
-
3(1)
C(9)
18(1)
29(1)
29(1)
9(1)
-
1(1)
0(1)
C(10)
22(1)
27(1)
20(1)
5(1)
2(1)
4(1)
C(11)
22(1)
22(1)
18(1)
4(1)
-
1(1)
2(1)
C(12)
22(1)
29(1)
19(1)
-
4(1)
1(1)
1(1)
______________________________________________________________________________
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
9
Table S5.
Hydrogen coordinates ( x 10
4
) and isotropic displacement
parameters (Å
2
x 10
3
)
for
S26
.
________________________________________________________________________________
x
y
z
U(eq)
________________________________________________________________________________
H(2A)
486
-
756
3589
34
H(2B)
375
680
4045
34
H(3A)
3116
-
496
3342
28
H(3B)
3045
410
4120
28
H(14)
2278
3331
5454
26
H(15)
2154
5178
6309
29
H(16)
1477
7361
5864
39
H(17)
867
7676
4562
47
H(18)
1073
5860
3693
34
H(7)
4835
4881
4478
25
H(8)
7563
5263
4313
29
H(9)
9001
4018
3400
30
H(10)
7734
2387
2620
28
H(12A)
5004
728
2646
28
H(12B)
4333
1970
2126
28
________________________________________________________________________________
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
10
Table
S
6.
Torsion angles [°] for
S26
.
________________________________________________________________
C(2)
-
O(1)
-
C(1)
-
O(2)
-
177.02(17)
C(2)
-
O(1)
-
C(1)
-
C(4)
2.5(2)
C(1)
-
O(1)
-
C(2)
-
C(3)
-
19.2(2)
O(1)
-
C(2)
-
C(3)
-
C(4)
27.33(19)
O(2)
-
C(1)
-
C(4)
-
C(5)
77.3(2)
O(1)
-
C(1)
-
C(4)
-
C(5)
-
102.15(16)
O(2)
-
C(1)
-
C(4)
-
C(3)
-
165.62(18)
O(1)
-
C(1)
-
C(4)
-
C(3)
14.92(18)
O(2)
-
C(1)
-
C(4)
-
C(12)
-
39.6(2)
O(1)
-
C(1)
-
C(4)
-
C(12)
140.99(16)
C(2)
-
C(3)
-
C(4)
-
C(1)
-
25.06(18)
C(2)
-
C(3)
-
C(4)
-
C(5)
90.60(18)
C(2)
-
C(3)
-
C(4)
-
C(12)
-
149.79(16)
C(1)
-
C(4)
-
C(5)
-
N(1)
43.2(2)
C(3)
-
C(4)
-
C(5)
-
N(1)
-
68.6(2)
C(12)
-
C(4)
-
C(5)
-
N(1)
165.55(15)
C(1)
-
C(4)
-
C(5)
-
C(6)
-
137.06(15)
C(3)
-
C(4)
-
C(5)
-
C(6)
111.15(16)
C(12)
-
C(4)
-
C(5)
-
C(6)
-
14.75(18)
C(6)
-
C(5)
-
N(1)
-
C(13)
-
1.7(3)
C(4)
-
C(5)
-
N(1)
-
C(13)
177.93(15)
C(5)
-
N(1)
-
C(13)
-
C(18)
97.1(2)
C(5)
-
N(1)
-
C(13)
-
C(14)
-
88.5(2)
C(18)
-
C(13)
-
C(14)
-
C(15)
-
2.5(3)
N(1)
-
C(13)
-
C(14)
-
C(15)
-
176.97(17)
C(13)
-
C(14)
-
C(15)
-
C(16)
1.5(3)
C(14)
-
C(15)
-
C(16)
-
C(17)
0.8(3)
C(15)
-
C(16)
-
C(17)
-
C(18)
-
2.0(4)
C(16)
-
C(17)
-
C(18)
-
C(13)
0.9(4)
C(14)
-
C(13)
-
C(18)
-
C(17)
1.3(3)
N(1)
-
C(13)
-
C(18)
-
C(17)
175.8(2)
N(1)
-
C(5)
-
C(6)
-
C(7)
8.8(3)
C(4)
-
C(5)
-
C(6)
-
C(7)
-
170.81(17)
N(1)
-
C(5)
-
C(6)
-
C(11)
-
172.14(18)
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
11
C(4)
-
C(5)
-
C(6)
-
C(11)
8.22(18)
C(11)
-
C(6)
-
C(7)
-
C(8)
-
1.1(3)
C(5)
-
C(6)
-
C(7)
-
C(8)
177.89(17)
C(6)
-
C(7)
-
C(8)
-
C(9)
0.4(3)
C(7)
-
C(8)
-
C(9)
-
C(10)
0.5(3)
C(8)
-
C(9)
-
C(10)
-
C(11)
-
0.8(3)
C(9)
-
C(10)
-
C(11)
-
C(6)
0.2(3)
C(9)
-
C(10)
-
C(11)
-
C(12)
179.75(18)
C(7)
-
C(6)
-
C(11)
-
C(10)
0.8(3)
C(5)
-
C(6)
-
C(11)
-
C(10)
-
178.39(16)
C(7)
-
C(6)
-
C(11)
-
C(12)
-
178.88(16)
C(5)
-
C(6)
-
C(11)
-
C(12)
2.0(2)
C(10)
-
C(11)
-
C(12)
-
C(4)
169.22(17)
C(6)
-
C(11)
-
C(12)
-
C(4)
-
11.2(2)
C(1)
-
C(4)
-
C(12)
-
C(11)
134.16(16)
C(5)
-
C(4)
-
C(12)
-
C(11)
15.33(18)
C(3)
-
C(4)
-
C(12)
-
C(11)
-
107.18(17)
________________________________________________________________
Symmetry transformations used to generate equivalent atoms:
X
-
Ray Structure Determination: Compound 13b
Figure S2.
X
-
ray coordinate of
13b
.
Ellipsoid contour % probability level: 50.
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
12
Low
-
temperature diffraction data (
f
-
and
w
-
scans) were collected on a Bruker AXS D8
VENTURE KAPPA diffractometer coupled to a PHOTON
II CPAD
detector with Cu
K
a
radiation
(
l
= 1.54178 Å) from an I
μ
S micro
-
source for the structure of compound
V24082
. The structure
was solved by direct methods using SHELXS
i
and refined against
F
2
on all data by full
-
matrix
least squares with SHELXL
-
201
9
ii
using established refinement techniques.
iii
All non
-
hydrogen
atoms were refined anisotropically. All hydrogen atoms were included into the model at
geometrically ca
lculated positions and refined using a riding model. The isotropic displacement
parameters of all hydrogen atoms were fixed to 1.2 times the
U
value of the atoms they are linked
to (1.5 times for methyl groups).
Compound
13b
crystallizes in the monoclinic space group
P
2
1
with one molecule in the
asymmetric unit.
Table S
7
.
Crystal data and structure refinement for
13b
.
Identification code
V24082
Empirical formula
C15 H16 O4
Formula weight
260.28
Temperature
100(2) K
Wavelength
1.54178 Å
Crystal system
Monoclinic
Space group
P2
1
Unit cell dimensions
a = 8.4789(9) Å
a
= 90°.
b = 10.7304(9) Å
b
= 102.577(7)°.
c = 13.9179(11) Å
g
= 90°.
Volume
1235.9(2) Å
3
Z
4
Density (calculated)
1.399 Mg/m
3
Absorption coefficient
0.833 mm
-
1
F(000)
552
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
13
Crystal size
0.300 x 0.200 x 0.200 mm
3
Theta range for data collection
3.253 to 74.518°.
Index ranges
-
10<=h<=9,
-
13<=k<=13,
-
16<=l<=17
Reflections collected
27571
Independent reflections
5037 [R(int) = 0.0380]
Completeness to theta = 67.679°
100.0 %
Absorption correction
Semi
-
empirical from equivalents
Max. and min. transmission
0.7538 and 0.6329
Refinement method
Full
-
matrix least
-
squares on F
2
Data / restraints / parameters
5037 / 1 / 345
Goodness
-
of
-
fit on F
2
1.027
Final R indices [I>2sigma(I)]
R1 = 0.0275, wR2 = 0.0706
R indices (all data)
R1 = 0.0282, wR2 = 0.0709
Absolute structure parameter
-
0.02(7)
Extinction coefficient
n/a
Largest diff. peak and hole
0.178 and
-
0.183 e.Å
-
3
Table S8.
Atomic coordinates ( x 10
4
) and equivalent isotropic
displacement parameters (Å
2
x
10
3
)
for
13b
. U(eq) is defined as one third of the trace of the orthogonalized U
ij
tensor.
________________________________________________________________________________
x
y
z
U(eq)
________________________________________________________________________________
C(1)
12956(2)
5769(2)
9952(1)
17(1)
O(1)
14128(2)
4949(1)
9898(1)
21(1)
O(2)
13245(2)
6814(1)
10248(1)
24(1)
C(2)
11270(2)
5190(2)
9598(1)
13(1)
C(3)
10646(2)
5783(2)
8574(1)
13(1)
O(3)
11507(1)
5741(1)
7978(1)
18(1)
C(4)
9095(2)
6486(2)
8360(1)
14(1)
C(5)
9059(2)
7622(2)
7854(1)
14(1)
C(6)
7666(2)
8330(2)
7646(1)
14(1)
C(7)
6271(2)
7899(2)
7920(1)
14(1)
O(4)
4983(2)
8674(1)
7700(1)
18(1)
C(8)
3478(2)
8266(2)
7903(2)
21(1)
C(9)
6274(2)
6739(2)
8384(1)
15(1)
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
14
C(10)
7691(2)
6038(2)
8618(1)
14(1)
C(11)
7711(2)
4788(2)
9118(1)
16(1)
C(12)
8634(2)
4817(2)
10198(1)
19(1)
C(13)
10260(2)
5492(2)
10357(1)
15(1)
C(14)
11676(2)
3800(2)
9511(1)
16(1)
C(15)
13435(2)
3807(2)
9413(1)
21(1)
C(21)
7963(2)
4268(2)
4940(1)
17(1)
O(5)
9174(2)
5098(1)
5016(1)
21(1)
O(6)
8013(2)
3258(1)
4575(1)
25(1)
C(22)
6570(2)
4800(2)
5364(1)
14(1)
C(23)
6784(2)
4161(2)
6378(1)
14(1)
O(7)
8151(2)
4110(1)
6894(1)
19(1)
C(24)
5413(2)
3523(2)
6680(1)
14(1)
C(25)
5766(2)
2416(2)
7216(1)
16(1)
C(26)
4561(2)
1703(2)
7462(1)
17(1)
C(27)
2957(2)
2102(2)
7172(1)
16(1)
O(8)
1852(2)
1316(1)
7426(1)
21(1)
C(28)
179(2)
1589(2)
7062(2)
22(1)
C(29)
2587(2)
3236(2)
6685(1)
15(1)
C(30)
3810(2)
3958(2)
6440(1)
14(1)
C(31)
3429(2)
5216(2)
5960(1)
16(1)
C(32)
3499(2)
5214(2)
4865(1)
18(1)
C(33)
4963(2)
4525(2)
4645(1)
16(1)
C(34)
7026(2)
6191(2)
5480(1)
16(1)
C(35)
8853(2)
6191(2)
5566(1)
19(1)
________________________________________________________________________________
Table S9.
Bond lengths [Å] and angles [°] for
13b
.
_____________________________________________________
C(1)
-
O(2)
1.201(2)
C(1)
-
O(1)
1.342(2)
C(1)
-
C(2)
1.538(2)
O(1)
-
C(15)
1.459(2)
C(2)
-
C(13)
1.533(2)
C(2)
-
C(14)
1.541(2)
C(2)
-
C(3)
1.546(2)
C(3)
-
O(3)
1.220(2)
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
15
C(3)
-
C(4)
1.488(2)
C(4)
-
C(10)
1.401(2)
C(4)
-
C(5)
1.405(2)
C(5)
-
C(6)
1.381(2)
C(5)
-
H(5)
0.9500
C(6)
-
C(7)
1.398(2)
C(6)
-
H(6)
0.9500
C(7)
-
O(4)
1.354(2)
C(7)
-
C(9)
1.402(2)
O(4)
-
C(8)
1.434(2)
C(8)
-
H(8A)
0.9800
C(8)
-
H(8B)
0.9800
C(8)
-
H(8C)
0.9800
C(9)
-
C(10)
1.395(2)
C(9)
-
H(9)
0.9500
C(10)
-
C(11)
1.510(2)
C(11)
-
C(12)
1.536(2)
C(11)
-
H(11A)
0.9900
C(11)
-
H(11B)
0.9900
C(12)
-
C(13)
1.530(2)
C(12)
-
H(12A)
0.9900
C(12)
-
H(12B)
0.9900
C(13)
-
H(13A)
0.9900
C(13)
-
H(13B)
0.9900
C(14)
-
C(15)
1.528(2)
C(14)
-
H(14A)
0.9900
C(14)
-
H(14B)
0.9900
C(15)
-
H(15A)
0.9900
C(15)
-
H(15B)
0.9900
C(21)
-
O(6)
1.200(2)
C(21)
-
O(5)
1.347(2)
C(21)
-
C(22)
1.541(2)
O(5)
-
C(35)
1.458(2)
C(22)
-
C(33)
1.533(2)
C(22)
-
C(34)
1.542(2)
C(22)
-
C(23)
1.543(2)
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
16
C(23)
-
O(7)
1.224(2)
C(23)
-
C(24)
1.487(2)
C(24)
-
C(25)
1.400(2)
C(24)
-
C(30)
1.406(2)
C(25)
-
C(26)
1.378(3)
C(25)
-
H(25)
0.9500
C(26)
-
C(27)
1.399(2)
C(26)
-
H(26)
0.9500
C(27)
-
O(8)
1.363(2)
C(27)
-
C(29)
1.395(3)
O(8)
-
C(28)
1.429(2)
C(28)
-
H(28A)
0.9800
C(28)
-
H(28B)
0.9800
C(28)
-
H(28C)
0.9800
C(29)
-
C(30)
1.396(2)
C(29)
-
H(29)
0.9500
C(30)
-
C(31)
1.510(2)
C(31)
-
C(32)
1.539(2)
C(31)
-
H(31A)
0.9900
C(31)
-
H(31B)
0.9900
C(32)
-
C(33)
1.532(2)
C(32)
-
H(32A)
0.9900
C(32)
-
H(32B)
0.9900
C(33)
-
H(33A)
0.9900
C(33)
-
H(33B)
0.9900
C(34)
-
C(35)
1.528(2)
C(34)
-
H(34A)
0.9900
C(34)
-
H(34B)
0.9900
C(35)
-
H(35A)
0.9900
C(35)
-
H(35B)
0.9900
O(2)
-
C(1)
-
O(1)
122.21(16)
O(2)
-
C(1)
-
C(2)
126.41(16)
O(1)
-
C(1)
-
C(2)
111.39(15)
C(1)
-
O(1)
-
C(15)
110.38(14)
C(13)
-
C(2)
-
C(1)
108.27(14)
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
17
C(13)
-
C(2)
-
C(14)
115.23(14)
C(1)
-
C(2)
-
C(14)
102.06(13)
C(13)
-
C(2)
-
C(3)
114.68(14)
C(1)
-
C(2)
-
C(3)
103.70(13)
C(14)
-
C(2)
-
C(3)
111.36(14)
O(3)
-
C(3)
-
C(4)
121.13(15)
O(3)
-
C(3)
-
C(2)
118.41(15)
C(4)
-
C(3)
-
C(2)
120.24(14)
C(10)
-
C(4)
-
C(5)
119.96(15)
C(10)
-
C(4)
-
C(3)
122.53(15)
C(5)
-
C(4)
-
C(3)
117.49(14)
C(6)
-
C(5)
-
C(4)
120.42(15)
C(6)
-
C(5)
-
H(5)
119.8
C(4)
-
C(5)
-
H(5)
119.8
C(5)
-
C(6)
-
C(7)
119.79(16)
C(5)
-
C(6)
-
H(6)
120.1
C(7)
-
C(6)
-
H(6)
120.1
O(4)
-
C(7)
-
C(6)
115.06(15)
O(4)
-
C(7)
-
C(9)
124.76(15)
C(6)
-
C(7)
-
C(9)
120.18(16)
C(7)
-
O(4)
-
C(8)
118.41(14)
O(4)
-
C(8)
-
H(8A)
109.5
O(4)
-
C(8)
-
H(8B)
109.5
H(8A)
-
C(8)
-
H(8B)
109.5
O(4)
-
C(8)
-
H(8C)
109.5
H(8A)
-
C(8)
-
H(8C)
109.5
H(8B)
-
C(8)
-
H(8C)
109.5
C(10)
-
C(9)
-
C(7)
120.05(15)
C(10)
-
C(9)
-
H(9)
120.0
C(7)
-
C(9)
-
H(9)
120.0
C(9)
-
C(10)
-
C(4)
119.50(15)
C(9)
-
C(10)
-
C(11)
120.57(15)
C(4)
-
C(10)
-
C(11)
119.90(15)
C(10)
-
C(11)
-
C(12)
112.65(14)
C(10)
-
C(11)
-
H(11A)
109.1
C(12)
-
C(11)
-
H(11A)
109.1
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
18
C(10)
-
C(11)
-
H(11B)
109.1
C(12)
-
C(11)
-
H(11B)
109.1
H(11A)
-
C(11)
-
H(11B)
107.8
C(13)
-
C(12)
-
C(11)
113.76(14)
C(13)
-
C(12)
-
H(12A)
108.8
C(11)
-
C(12)
-
H(12A)
108.8
C(13)
-
C(12)
-
H(12B)
108.8
C(11)
-
C(12)
-
H(12B)
108.8
H(12A)
-
C(12)
-
H(12B)
107.7
C(12)
-
C(13)
-
C(2)
114.91(14)
C(12)
-
C(13)
-
H(13A)
108.5
C(2)
-
C(13)
-
H(13A)
108.5
C(12)
-
C(13)
-
H(13B)
108.5
C(2)
-
C(13)
-
H(13B)
108.5
H(13A)
-
C(13)
-
H(13B)
107.5
C(15)
-
C(14)
-
C(2)
103.92(14)
C(15)
-
C(14)
-
H(14A)
111.0
C(2)
-
C(14)
-
H(14A)
111.0
C(15)
-
C(14)
-
H(14B)
111.0
C(2)
-
C(14)
-
H(14B)
111.0
H(14A)
-
C(14)
-
H(14B)
109.0
O(1)
-
C(15)
-
C(14)
105.38(14)
O(1)
-
C(15)
-
H(15A)
110.7
C(14)
-
C(15)
-
H(15A)
110.7
O(1)
-
C(15)
-
H(15B)
110.7
C(14)
-
C(15)
-
H(15B)
110.7
H(15A)
-
C(15)
-
H(15B)
108.8
O(6)
-
C(21)
-
O(5)
122.24(16)
O(6)
-
C(21)
-
C(22)
126.68(16)
O(5)
-
C(21)
-
C(22)
111.08(15)
C(21)
-
O(5)
-
C(35)
110.33(13)
C(33)
-
C(22)
-
C(21)
108.92(14)
C(33)
-
C(22)
-
C(34)
114.93(14)
C(21)
-
C(22)
-
C(34)
101.71(13)
C(33)
-
C(22)
-
C(23)
115.02(14)
C(21)
-
C(22)
-
C(23)
103.81(13)
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
19
C(34)
-
C(22)
-
C(23)
110.93(14)
O(7)
-
C(23)
-
C(24)
120.82(16)
O(7)
-
C(23)
-
C(22)
117.65(15)
C(24)
-
C(23)
-
C(22)
121.28(14)
C(25)
-
C(24)
-
C(30)
119.47(15)
C(25)
-
C(24)
-
C(23)
116.84(15)
C(30)
-
C(24)
-
C(23)
123.68(16)
C(26)
-
C(25)
-
C(24)
121.26(16)
C(26)
-
C(25)
-
H(25)
119.4
C(24)
-
C(25)
-
H(25)
119.4
C(25)
-
C(26)
-
C(27)
119.09(16)
C(25)
-
C(26)
-
H(26)
120.5
C(27)
-
C(26)
-
H(26)
120.5
O(8)
-
C(27)
-
C(29)
124.80(16)
O(8)
-
C(27)
-
C(26)
114.63(16)
C(29)
-
C(27)
-
C(26)
120.56(16)
C(27)
-
O(8)
-
C(28)
117.83(14)
O(8)
-
C(28)
-
H(28A)
109.5
O(8)
-
C(28)
-
H(28B)
109.5
H(28A)
-
C(28)
-
H(28B)
109.5
O(8)
-
C(28)
-
H(28C)
109.5
H(28A)
-
C(28)
-
H(28C)
109.5
H(28B)
-
C(28)
-
H(28C)
109.5
C(27)
-
C(29)
-
C(30)
120.17(15)
C(27)
-
C(29)
-
H(29)
119.9
C(30)
-
C(29)
-
H(29)
119.9
C(29)
-
C(30)
-
C(24)
119.26(16)
C(29)
-
C(30)
-
C(31)
120.36(15)
C(24)
-
C(30)
-
C(31)
120.32(15)
C(30)
-
C(31)
-
C(32)
112.70(14)
C(30)
-
C(31)
-
H(31A)
109.1
C(32)
-
C(31)
-
H(31A)
109.1
C(30)
-
C(31)
-
H(31B)
109.1
C(32)
-
C(31)
-
H(31B)
109.1
H(31A)
-
C(31)
-
H(31B)
107.8
C(33)
-
C(32)
-
C(31)
113.97(14)
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
20
C(33)
-
C(32)
-
H(32A)
108.8
C(31)
-
C(32)
-
H(32A)
108.8
C(33)
-
C(32)
-
H(32B)
108.8
C(31)
-
C(32)
-
H(32B)
108.8
H(32A)
-
C(32)
-
H(32B)
107.7
C(32)
-
C(33)
-
C(22)
114.85(14)
C(32)
-
C(33)
-
H(33A)
108.6
C(22)
-
C(33)
-
H(33A)
108.6
C(32)
-
C(33)
-
H(33B)
108.6
C(22)
-
C(33)
-
H(33B)
108.6
H(33A)
-
C(33)
-
H(33B)
107.5
C(35)
-
C(34)
-
C(22)
103.61(14)
C(35)
-
C(34)
-
H(34A)
111.0
C(22)
-
C(34)
-
H(34A)
111.0
C(35)
-
C(34)
-
H(34B)
111.0
C(22)
-
C(34)
-
H(34B)
111.0
H(34A)
-
C(34)
-
H(34B)
109.0
O(5)
-
C(35)
-
C(34)
105.11(13)
O(5)
-
C(35)
-
H(35A)
110.7
C(34)
-
C(35)
-
H(35A)
110.7
O(5)
-
C(35)
-
H(35B)
110.7
C(34)
-
C(35)
-
H(35B)
110.7
H(35A)
-
C(35)
-
H(35B)
108.8
_____________________________________________________________
Symmetry transformations used to generate equivalent atoms:
Table S10.
Anisotropic displacement parameters (Å
2
x 10
3
) for
13b
. The anisotropic
displacement factor exponent takes the form:
-
2
p
2
[ h
2
a*
2
U
11
+ ... + 2 h k a* b* U
12
]
______________________________________________________________________________
U
11
U
22
U
33
U
23
U
13
U
12
______________________________________________________________________________
C(1)
16(1)
21(1)
14(1)
2(1)
2(1)
-
1(1)
O(1)
14(1)
26(1)
23(1)
-
1(1)
4(1)
1(1)
O(2)
27(1)
20(1)
23(1)
-
3(1)
2(1)
-
7(1)
C(2)
12(1)
13(1)
14(1)
0(1)
3(1)
0(1)
C(3)
13(1)
12(1)
14(1)
-
1(1)
3(1)
-
3(1)
X
-
Ray Crystallography Data
for Stanko, Ramirez, de Almenara, Virgil, and Stoltz
S
21
O(3)
16(1)
21(1)
17(1)
2(1)
7(1)
2(1)
C(4)
14(1)
14(1)
13(1)
0(1)
3(1)
0(1)
C(5)
12(1)
16(1)
13(1)
-
1(1)
4(1)
-
4(1)
C(6)
18(1)
12(1)
13(1)
2(1)
2(1)
-
1(1)
C(7)
14(1)
14(1)
13(1)
-
1(1)
2(1)
1(1)
O(4)
15(1)
16(1)
24(1)
6(1)
6(1)
2(1)
C(8)
15(1)
20(1)
28(1)
6(1)
7(1)
3(1)
C(9)
15(1)
14(1)
16(1)
0(1)
5(1)
-
2(1)
C(10)
15(1)
15(1)
13(1)
1(1)
3(1)
0(1)
C(11)
14(1)
15(1)
22(1)
5(1)
7(1)
1(1)
C(12)
19(1)
20(1)
20(1)
7(1)
9(1)
4(1)
C(13)
19(1)
15(1)
13(1)
2(1)
6(1)
4(1)
C(14)
19(1)
12(1)
17(1)
1(1)
5(1)
1(1)
C(15)
21(1)
20(1)
22(1)
0(1)
7(1)
4(1)
C(21)
16(1)
20(1)
16(1)
0(1)
4(1)
2(1)
O(5)
17(1)
24(1)
22(1)
-
2(1)
8(1)
-
2(1)
O(6)
27(1)
21(1)
30(1)
-
7(1)
9(1)
5(1)
C(22)
14(1)
14(1)
15(1)
-
1(1)
4(1)
1(1)
C(23)
15(1)
11(1)
16(1)
-
1(1)
3(1)
2(1)
O(7)
15(1)
20(1)
20(1)
3(1)
0(1)
0(1)
C(24)
17(1)
13(1)
14(1)
-
2(1)
3(1)
0(1)
C(25)
14(1)
16(1)
17(1)
0(1)
2(1)
2(1)
C(26)
20(1)
14(1)
17(1)
2(1)
4(1)
1(1)
C(27)
17(1)
15(1)
16(1)
-
1(1)
6(1)
-
2(1)
O(8)
17(1)
19(1)
29(1)
6(1)
8(1)
-
1(1)
C(28)
16(1)
23(1)
26(1)
2(1)
7(1)
-
3(1)
C(29)
14(1)
16(1)
16(1)
-
2(1)
4(1)
1(1)
C(30)
16(1)
13(1)
12(1)
-
2(1)
4(1)
1(1)
C(31)
14(1)
13(1)
19(1)
2(1)
4(1)
3(1)
C(32)
16(1)
18(1)
18(1)
4(1)
3(1)
1(1)
C(33)
16(1)
17(1)
14(1)
0(1)
2(1)
-
2(1)
C(34)
18(1)
14(1)
18(1)
0(1)
5(1)
-
1(1)
C(35)
18(1)
18(1)
21(1)
-
1(1)
4(1)
-
4(1)
______________________________________________________________________________